Water → HCID 68429363、化合物

HRID 2191283ノート

反応式

HRID 2191283 の反応式
[CH3:1][CH:2]([CH3:6])[C@@H:3]([OH:5])[CH3:4].[H-].[Na+].Cl[C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][O:18][C:19]=2[N:20]=1.O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:4][C@H:3]([O:5][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][O:18][C:19]=2[N:20]=1)[CH:2]([CH3:6])[CH3:1]

参加物

8

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6999784(S)-(+)-3-Methyl-2-butanolHCID 57356939Tert-butyl 8-chloro-2,3-dihydropyrido[3,2-F][1,4]oxazepine-4(5H)-carboxylate

生成物 1

HCID 68429363HCID 68429363、化合物収率 67%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回

反応条件

温度
70 °C

実験手順

To a solution of (2S)-3-methylbutan-2-ol (0.38 mL) in toluene (8 mL) was added sodium hydride (0.28 g), and the resulting mixture was stirred at 70° C. for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (1.0 g), BINAP (0.066 g), Pd2(dba)3 (0.048 g) and toluene (8 mL) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give tert-butyl 8-{[(1S)-1,2-dimethylpropyl]oxy}-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.79 g, 67%) as a white powder.

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere
  3. extractionthe resulting product was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-9e4cee0c179e46ddbd717bf1afa21841
出典データセット
uspto-grants-2012_12
特許番号
US08329687B2

反応ノート

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